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Issue 37, 2019
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A base-promoted cascade reaction of α,β-unsaturated N-tosylhydrazones with o-hydroxybenzyl alcohols: highly regioselective synthesis of N-sec-alkylpyrazoles

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Abstract

An efficient method for the synthesis of N-sec-alkylpyrazoles through a base-promoted cascade cyclization/Michael addition reaction of α,β-unsaturated N-tosylhydrazones with ortho-hydroxybenzyl alcohols has been developed. The desired products containing di- or triaryl groups at the same carbon atom were afforded in good to excellent yields with excellent regioselectivities (>20 : 1). Moreover, a three-component reaction of ortho-hydroxybenzyl alcohols, α,β-unsaturated N-tosylhydrazones and saturated N-tosylhydrazones also took place to afford pyrazoles in good yields. This reaction offers a new route to triarylmethanes with a simple operation and is applicable for large-scale synthesis.

Graphical abstract: A base-promoted cascade reaction of α,β-unsaturated N-tosylhydrazones with o-hydroxybenzyl alcohols: highly regioselective synthesis of N-sec-alkylpyrazoles

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Publication details

The article was received on 13 Aug 2019, accepted on 04 Sep 2019 and first published on 05 Sep 2019


Article type: Paper
DOI: 10.1039/C9OB01780A
Org. Biomol. Chem., 2019,17, 8561-8570

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    A base-promoted cascade reaction of α,β-unsaturated N-tosylhydrazones with o-hydroxybenzyl alcohols: highly regioselective synthesis of N-sec-alkylpyrazoles

    L. Chen, J. Zhao, A. Xia, X. Guo, Y. Gan, C. Zhou, Z. Yang, J. Yang and T. Kang, Org. Biomol. Chem., 2019, 17, 8561
    DOI: 10.1039/C9OB01780A

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